HCID 22066011, compound → HCID 22066009, compound

Participants

Reaction Steps

The solution of compound (3) (50 mg) in acetic acid-sulfuric acid solution (96:4, 5 ml) was refluxed for 1 hour under nitrogen. After cooling to room temperature, the solution was evaporated under vacuum. The residue was neutralized with ammonia water and extracted with chloroform (100 ml ×2). The combined chloroform layers were washed with water (50 ml×2), dried over anhydrous sodium sulfate, concentrated under reduced pressure. The residue obtained was purified on a silica gel column and eluted with chloroform-methanol (99:3) to obtain a brown solid, 9-hydroxy-2-isopropyloxy-1,10-dimethoxy-7-oxoaporphine (4) (10 mg, 22% yield): m.p. 240–242° C.; IR(KBr) νmax 3422, 3008, 2977, 2932, 1728, 1651, 1593, 1513, 1461, 1417, 1380, 1351, 1280, 1247, 1213, 1149, 1116, 1059, 1013, 932, 894, 866, 822 cm−1; 1H NMR (200 MHz, CD3OD) δ 1.51 (6H, d, J=6.0 Hz, 2×CH3), 4.01 (3H, s, OCH3), 4.02 (3H, s, OCH3), 4.87 (1H, m, OCH), 7.25 (1H, s, H-3), 7.74 (1H, s, H-8), 7.83 (1H, d, J=4.8 Hz, H-4), 8.63 (1H, d, J=4.8 Hz, H-5), 8.68 (1H, s, H-11); ESI MS (positive): [M+H]+ 366.

Provenance & Evidence